194350-71-5Relevant academic research and scientific papers
Copper-Mediated Diastereoselective C-H Thiolation of Ferrocenes
Kong, Wei-Jun,Shao, Qian,Li, Ming-Hong,Zhou, Zeng-Le,Xu, Hui,Dai, Hui-Xiong,Yu, Jin-Quan
, p. 2832 - 2836 (2018)
The first copper-mediated diastereoselective C-H thiolation of ferrocenes has been developed. A chiral oxazoline directing group with tert-butyl substituent is essential to the high diastereoselectivity ratio and the suppression of overreaction of monothi
Design, Synthesis, Fungicidal Activity, and Unexpected Docking Model of the First Chiral Boscalid Analogues Containing Oxazolines
Li, Shengkun,Li, Dangdang,Xiao, Taifeng,Zhang, Shasha,Song, Zehua,Ma, Hongyu
, p. 8927 - 8934 (2016/12/07)
Chirality greatly influences the biological and pharmacological properties of a pesticide and will contribute to unnecessary environmental loading and undesired ecological impact. No structure and activity relationship (SAR) of enantiopure succinate dehydrogenase inhibitors (SDHIs) was documented during the structure optimization of boscalids. On the basis of commercial SDHIs, oxazoline natural products, and versatile oxazoline ligands in organic synthesis, the first effort was devoted to explore the chiral SDHIs and the preliminary mechanism thereof. Fine-tuning furnished chiral nicotinamides 4ag as a more promising fungicidal candidate against Rhizoctonia solani, Botrytis cinerea, and Sclerotinia sclerotiorum, with EC50 values of 0.58, 0.42, and 2.10 mg/L, respectively. In vivo bioassay and molecular docking were investigated to explore the potential in practical application and plausible novelty in action mechanism, respectively. The unexpected molecular docking model showed the different chiral effects on the binding site with the amino acid residues. This chiral nicotinamide also featured easy synthesis and cost-efficacy. It will provide a powerful complement to the commercial SDHI fungicides with the introduction of chirality.
Oxazolines as Dual-Function Traceless Chromophores and Chiral Auxiliaries: Enantioselective Photoassisted Synthesis of Polyheterocyclic Ketones
Mukhina, Olga A.,Kutateladze, Andrei G.
supporting information, p. 2110 - 2113 (2016/03/05)
2-(o-Amidophenyl)oxa- and -thiazolines undergo excited-state intramolecular proton transfer (ESIPT), generating aza-o-xylylenes capable of intramolecular [4+2] and [4+4] cycloadditions with tethered unsaturated pendants. Facile hydrolysis of the primary p
Chiral oxazoline ligands containing a 1,2,4-triazine ring and their application in the Cu-catalyzed asymmetric Henry reaction
Wolińska, Ewa
, p. 7269 - 7278 (2013/08/23)
Eleven members of new ligand class incorporating a chiral oxazoline and a 1,2,4-triazine ring have been synthesized via Pd-catalyzed amination reaction of 3-halo-1,2,4-triazines with 2-(o-aminophenyl)oxazolines. Buchwald-Hartwig amination of 3-halo-1,2,4-triazines was investigated to establish the best conditions for synthesis of the title ligands. Catalytic activity of the new ligands was evaluated in the asymmetric Henry reaction of nitromethane with a variety of aromatic and aliphatic aldehydes. The β-hydroxy nitroalkanes were obtained in high yields (up to 95%), and moderate-to-good enantioselectivity (up to 82% ee).
Chiral primary amine catalyzed asymmetric epoxidation of α-substituted acroleins
Li, Jiuyuan,Fu, Niankai,Zhang, Long,Zhou, Pengxin,Luo, Sanzhong,Cheng, Jin-Pei
experimental part, p. 6840 - 6849 (2011/03/19)
1,1-Disubstituted terminal alkenes remain challenging substrates in asymmetric epoxidation reactions. In this study, chiral primary amines are shown to catalyze the asymmetric epoxidation of α-substituted acroleins, a versatile type of 1,1-disubstituted t
The synthesis of new oxazoline-containing bifunctional catalysts and their application in the addition of diethylzinc to aldehydes
Coeffard, Vincent,Mueller-Bunz, Helge,Guiry, Patrick J.
experimental part, p. 1723 - 1734 (2009/06/27)
The straightforward preparation of new modular oxazoline-containing bifunctional catalysts is reported employing a microwave-assisted Buchwald-Hartwig aryl amination as the key step. Covalent attachment of 2-(o-aminophenyl)oxazolines and pyridine derivati
New thiazoline-oxazoline ligands and their application in the asymmetric friedel-crafts reaction
McKeon, Sean C.,Mueller-Bunz, Helge,Guiry, Patrick J.
body text, p. 4833 - 4841 (2010/02/28)
Six members of a novel non-C2-symmetric ligand class incorporating an oxazoline and. thiazoline unit have been prepared in a four-step, high-yielding and. convergent: synthesis, in which the key step is a microwave-assisted palladium-catalyzed
Further improvement on sulfonamide-based ligand for catalytic asymmetric 2-haloallylation and allylation
Zhang, Zhiyu,Huang, Jian,Ma, Bin,Kishi, Yoshito
supporting information; experimental part, p. 3073 - 3076 (2009/05/11)
(Chemical Equation Presented) The sulfonamide-based ligand B was found to exhibit an outstanding crystallinity and perform well as a ligand for Cr-mediated catalytic asymmetric 2-haloallylation and allylation. The new ligand has an appealing advantage ove
Synthesis of non-symmetric bis(oxazoline)-containing ligands and their application in the catalytic enantioselective Nozaki-Hiyama-Kishi allylation of benzaldehyde
Hargaden, Grainne C.,O'Sullivan, Timothy P.,Guiry, Patrick J.
scheme or table, p. 562 - 566 (2008/10/09)
We report the good to high-yielding three-step synthesis of non-symmetrical bis(oxazoline)-containing ligands possessing an N-thienylaniline unit. The convergent synthesis employed a palladium-catalysed aryl amination of 2-(2′-bromothiophene)nitrile as th
Oxazoline-substituted prolinamide-based organocatalysts for the direct intermolecular aldol reaction between cyclohexanone and aromatic aldehydes
Doherty, Simon,Knight, Julian G.,McRae, Amy,Harrington, Ross W.,Clegg, William
scheme or table, p. 1759 - 1766 (2009/04/06)
Oxazoline-substituted prolinamides catalyse the direct asymmetric aldol reaction between cyclohexanone and a range of aldehydes to give excellent conversions and enantioselectivities up to 84% under optimum conditions. Reactions were highly substrate-spec
